KR101802574B1 - Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same - Google Patents
Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same Download PDFInfo
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- KR101802574B1 KR101802574B1 KR1020150037718A KR20150037718A KR101802574B1 KR 101802574 B1 KR101802574 B1 KR 101802574B1 KR 1020150037718 A KR1020150037718 A KR 1020150037718A KR 20150037718 A KR20150037718 A KR 20150037718A KR 101802574 B1 KR101802574 B1 KR 101802574B1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices with at least one potential-jump barrier or surface barrier specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices with at least one potential-jump barrier or surface barrier specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
Abstract
A photo-curable monomer, a silicone-containing monomer, and an initiator, wherein the silicon-containing monomer is represented by Formula 1, and an organic light emitting diode display device manufactured from the composition.
Description
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition for encapsulating an organic light emitting device and an organic light emitting diode display device manufactured therefrom.
The organic light emitting element display device is a light emitting display device, and includes an organic light emitting element. When the organic light emitting device is in contact with external moisture or oxygen, the light emitting property may be deteriorated, and the organic light emitting device should be sealed with a sealing composition. The organic light emitting device is encapsulated in a multi-layered structure in which an inorganic barrier layer and an organic barrier layer are sequentially formed. The inorganic barrier layer is formed by plasma deposition, and the organic barrier layer can be etched by plasma. Such an etching may damage the sealing function of the organic barrier layer, and the organic light emitting device may have poor light emitting properties and low reliability. In this regard, Korean Patent Publication No. 2011-0071039 discloses a sealing method of an organic light emitting device.
SUMMARY OF THE INVENTION An object of the present invention is to provide a composition for encapsulating an organic light emitting device capable of realizing an organic barrier layer having a strong resistance to plasma and improving the reliability of the organic light emitting device.
Another object of the present invention is to provide a composition for encapsulating an organic light emitting device which can realize an organic barrier layer having a high photo-curability and a high light transmittance.
The composition for encapsulating an organic light emitting diode of the present invention comprises a photo-curable monomer, a monomer containing silicon and an initiator, and the monomer containing silicon may be represented by the following formula (1)
≪ Formula 1 >
(Wherein R 1 , R 2 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , Y 1 , Y 2 , and n are as defined in the detailed description below).
The organic electroluminescent display device of the present invention includes an organic light emitting device and a barrier stack formed on the organic light emitting device and including an inorganic barrier layer and an organic barrier layer, .
The present invention provides a composition for encapsulating an organic light emitting device capable of realizing an organic barrier layer having a strong resistance to plasma and improving the reliability of the organic light emitting device.
The present invention provides an organic light emitting device encapsulation composition capable of realizing an organic barrier layer having a high photo-curability and a high light transmittance.
1 is a cross-sectional view of an OLED display device according to an embodiment of the present invention.
2 is a cross-sectional view of an OLED display device according to another embodiment of the present invention.
The present invention will now be described more fully hereinafter with reference to the accompanying drawings, in which preferred embodiments of the invention are shown. The present invention may be embodied in many different forms and is not limited to the embodiments described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and the same or similar components are denoted by the same reference numerals throughout the specification.
As used herein, " (meth) acrylic " may mean acrylic and / or methacrylic.
As used herein, " substituted " means that at least one hydrogen atom of the functional group of the present invention is substituted with at least one substituent selected from the group consisting of a halogen (F, Cl, Br or I), a hydroxy group, a nitro group, a cyano group, , = NR, R is an alkyl group having a carbon number of 1-10), an amino group (-NH 2, -NH (R ' ), -N (R ") (R"'), R ', R ", R"' is A hydrazine or hydrazone group, a carboxy group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms , Or a heterocycloalkyl group having 2 to 30 carbon atoms.
The composition for encapsulating an organic light emitting diode according to an embodiment of the present invention includes a photo-curable monomer, a monomer containing silicon, and an initiator, and the monomer containing silicon may be represented by the following formula (1). By including the silicon-containing monomer, it is possible to realize an organic barrier layer which has a strong resistance to plasma and improves the reliability of the organic light emitting device. In the present invention, photo-curable monomers, silicon-containing monomers and initiators are different compounds.
Hereinafter, photocurable monomers, silicon-containing monomers and initiators will be described in detail.
Photocurable monomer
Photocurable monomers may include photocurable monomers, other than silicon containing monomers. Specifically, the photocurable monomer may refer to a non-silicon photocurable monomer having no photocurable functional group (e.g., (meth) acrylate group, vinyl group, etc.) without silicon.
The photocurable monomer can be a monofunctional monomer, a multifunctional monomer, or a mixture thereof. As used herein, "monofunctional monomer" may refer to a monomer having one photocurable functional group. As used herein, "multifunctional monomer" may refer to a monomer having two or more photocurable functional groups. For example, photocurable monomers may include monomers having 1 to 30 photocurable functional groups, specifically 1 to 20, specifically 1 to 6 photocurable functional groups.
The photocurable monomer is an aromatic compound having 6 to 20 carbon atoms and having a substituted or unsubstituted vinyl group; An alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or an unsaturated carboxylic acid ester having a hydroxy group and an alkyl group having 1 to 20 carbon atoms; An unsaturated carboxylic acid ester having an aminoalkyl group having from 1 to 20 carbon atoms; Vinyl esters of saturated or unsaturated carboxylic acids having from 1 to 20 carbon atoms; Unsaturated carboxylic acid glycidyl esters having 1 to 20 carbon atoms; Vinyl cyanide compounds; Unsaturated amide compounds; Monofunctional (meth) acrylates of monohydric alcohols or polyhydric alcohols; (Meth) acrylate of a monoalcohol or a polyhydric alcohol. The above "polyhydric alcohol" may mean an alcohol having two or more hydroxyl groups and having 2 to 20, specifically 2 to 10, particularly 2 to 6 alcohols. As used herein, "monofunctional (meth) acrylate" may mean a monomer having one (meth) acrylate group. As used herein, "multifunctional (meth) acrylate" may mean a monomer having two or more (meth) acrylate groups.
In an embodiment, the photocurable monomer is an aromatic compound having 6 to 20 carbon atoms and having an alkenyl group including a vinyl group such as styrene, alpha-methylstyrene, vinyltoluene, vinylbenzyl ether, and vinylbenzyl methyl ether; (Meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (Meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, decyl (meth) acrylate, Unsaturated carboxylic acid esters such as acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl esters such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Saturated or unsaturated carboxylic acid vinyl esters such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl esters having 1 to 20 carbon atoms such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; (Meth) acrylamide, and the like.
In embodiments, the photocurable monomer may be a monofunctional (meth) acrylate of a monoalcohol or a polyhydric alcohol; Polyfunctional (meth) acrylates of monohydric alcohols, monoalcohols or polyhydric alcohols.
More specifically, the photo-curable monomer is selected from the group consisting of methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) (Meth) acrylate such as decanyl (meth) acrylate, undecanyl (meth) acrylate, dodecyl (meth) acrylate, cyclohexyl Mono (meth) acrylates of 30 monoalcohols; Acrylate, triethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tri (propylene glycol) di (meth) acrylate, diethylene glycol di (Meth) acrylate or polyalkylene glycol di (meth) acrylate, or mixtures thereof, comprising at least one of poly (propylene glycol) di (meth) acrylate and poly Acrylate, 1,6-hexanediol di (meth) acrylate, octanediol di (meth) acrylate, nonanediol di (meth) acrylate, decanediol di (Meth) acrylate, dodecanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, dipentaerythritol di Di (meth) acrylates of diols, triols, tetraols, pentahols or hexahols having 2 to 20 carbon atoms, including acrylates and the like; Tetraol, tetraol, pentanol or hexa (meth) acrylate having 3 to 20 carbon atoms such as trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri Tri (meth) acrylate; Tetra (meth) acrylate of tetraol, pentanol or hexanol having 4 to 20 carbon atoms, including pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate and the like; Penta (meth) acrylate of pentanol or hexanol having 4 to 20 carbon atoms, including dipentaerythritol penta (meth) acrylate; Hexa (meth) acrylates of hexa-olefins having 4 to 20 carbon atoms such as dipentaerythritol hexa (meth) acrylate and the like; Bisphenol A di (meth) acrylate; Novolak epoxy (meth) acrylate, and the like.
The photocurable monomers may be included singly or in combination of two or more. The photocurable monomers may be used singly or in combination of two or more of the same types.
Photocurable monomers may comprise a mixture of monofunctional monomers and polyfunctional monomers. The monofunctional monomer: polyfunctional monomer in the mixture may be included in a weight ratio of 1: 0.1 to 1:20, specifically 1: 0.5 to 1:10 by weight.
The photocurable monomer includes at least one of a polyfunctional (meth) acrylate such as a bifunctional (meth) acrylate, a trifunctional (meth) acrylate and a tetrafunctional (meth) acrylate, This low organic barrier layer can be realized.
Photocurable monomers include: a) bifunctional (meth) acrylates; And b) a mixture of at least one of a trifunctional (meth) acrylate, a tetrafunctional (meth) acrylate, and the like. The weight ratio of at least one of a) bifunctional (meth) acrylate: b) trifunctional (meth) acrylate and tetrafunctional (meth) acrylate may be from 1: 2 to 1: 5. In the above range, an organic barrier layer having a low etching rate by plasma can be realized.
In one embodiment of the invention, the photocurable monomer may comprise one or more of i), ii), iii), iv), v)
(i) mono (meth) acrylates of monohydric alcohols having 1 to 30 carbon atoms,
ii) monoalkyleneglycol di (meth) acrylate or polyalkylene glycol di (meth) acrylate or mixtures thereof,
iii) di (meth) acrylates of 2 to 20 carbon atoms, diols, triols, tetraols, pentaols, or hexaols,
iv) tri (meth) acrylates of triols having from 3 to 20 carbon atoms, such as triols, tetraols, pentaols or hexaols,
v) tetra (meth) acrylates of tetraol, pentanol or hexanol having from 4 to 20 carbon atoms.
In one embodiment of the invention, the photocurable monomer may comprise the following components:
ii) monoalkyleneglycol di (meth) acrylate or polyalkylene glycol di (meth) acrylate or mixtures thereof; And
iii) a di (meth) acrylate of a diol, triol, tetraol, pentanol or hexanol of 2 to 20 carbon atoms, iv) a tri (meth) acrylate of a triol, tetraol, pentanol or hexanol Tri (meth) acrylate, v) tetra (meth) acrylate of tetraol, pentanol or hexanol having 4-20 carbon atoms.
In one embodiment of the invention, the photocurable monomer may comprise the following components:
ii) monoalkyleneglycol di (meth) acrylate or polyalkylene glycol di (meth) acrylate or mixtures thereof; And
iii) di (meth) acrylates of 2 to 20 carbon atoms, diols, triols, tetraols, pentaols, or hexaols.
In one embodiment of the invention, the photocurable monomer may comprise the following components:
ii) monoalkyleneglycol di (meth) acrylate or polyalkylene glycol di (meth) acrylate or mixtures thereof;
iii) di (meth) acrylates of 2 to 20 carbon atoms, such as diols, triols, tetraols, pentahols or hexaols; And
iv) tri (meth) acrylates of triols, triols, tetraols, pentaols or hexaols of 3 to 20 carbon atoms, v) tetra (meth) acrylates of tetra One or more of.
In one embodiment of the invention, the photocurable monomer may comprise the following components:
ii) monoalkyleneglycol di (meth) acrylate or polyalkylene glycol di (meth) acrylate or mixtures thereof;
iii) di (meth) acrylates of 2 to 20 carbon atoms, such as diols, triols, tetraols, pentahols or hexaols; And
v) tetra (meth) acrylates of tetraol, pentanol or hexanol having 4-20 carbon atoms.
The i), ii), iii), iv), and v) may be included in the composition for encapsulating an organic luminescent element, either singly or in combination.
The above ii) can compensate the physical properties of other photocurable monomers having a relatively high viscosity by increasing the storage modulus after curing, lowering the hardening shrinkage rate, and lowering the viscosity of the composition. By further including at least one of iii), iv) and v) in the ii) above, an organic barrier layer having a low etching rate by plasma can be realized.
The above-mentioned ii) may be contained in an amount of 10% by weight to 80% by weight, specifically 10% by weight to 60% by weight, based on the total weight of the photocurable monomer, the silicon-containing monomer and the initiator. In the above range, the composition can lower the outgas and the moisture permeability that can be generated from the plasma generated during the manufacture of the thin film encapsulation layer, and can realize the organic barrier layer having a small etching rate for the plasma.
Iii) is 10% by weight to 80% by weight, specifically 30% by weight to 70% by weight, more preferably 30% by weight or less, based on the total weight of the photocurable monomer, the silicon- 60% by weight. In the above range, the composition can lower the outgas and the moisture permeability that can be generated from the plasma generated during the manufacture of the thin film encapsulation layer, and can realize the organic barrier layer having a small etching rate for the plasma.
The above v) is 0% by weight to 50% by weight, specifically 0% by weight to 20% by weight, more specifically 0% by weight, more preferably 0% by weight, based on the total weight of the photocurable monomer, 10% by weight. In the above range, the composition can lower the outgas and the moisture permeability that can be generated from the plasma generated during the manufacture of the thin film encapsulation layer, and can realize the organic barrier layer having a small etching rate for the plasma.
The photocurable monomer may be contained in an amount of 10 to 80% by weight, specifically 50 to 75% by weight, based on the total weight of the photocurable monomer, the silicon-containing monomer and the initiator. In the above range, the composition can lower the outgas and the moisture permeability that can be generated from the plasma generated during the manufacture of the thin film encapsulation layer, and can realize the organic barrier layer having a small etching rate for the plasma.
Silicon-containing monomers
The silicon-containing monomer may be a silicon-based photo-curable monomer containing silicon and having photo-curable functional groups at both ends. For example, the photocurable functional group may be a substituted or unsubstituted vinyl group or (meth) acrylate group.
In embodiments, the silicone-containing monomer may be represented by the formula:
≪ Formula 1 >
(Wherein R 1 and R 2 are the same or different and each represents a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted alkylene ether group having 1-30 carbon atoms, Wherein R 'is a substituted or unsubstituted alkyl group having 1-30 carbon atoms, and R "is a substituted or unsubstituted alkylene group having 1-20 carbon atoms, A substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylene group having 7 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 7 to 30 carbon atoms, or * -OR " Or an unsubstituted or substituted alkylene group having 1-20 carbon atoms)
X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are the same or different and represent hydrogen, a substituted or unsubstituted alkyl group having 1-30 carbon atoms, a substituted or unsubstituted alkyl ether group having 1-30 carbon atoms , * -N (R ') (R ") wherein * is the connecting site of the element, R' and R" are the same or different and represent hydrogen or a substituted or unsubstituted alkyl group having 1-30 carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms,
At least one of X 1 , X 2 , X 3 , X 4 , X 5 and X 6 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Y 1, Y 2 are the same or different, to a (2),
(2)
(Wherein, * is the connecting site of the element and Z is hydrogen or a substituted or unsubstituted alkyl group having 1-30 carbon atoms)
n is an integer from 0 to 30, or the average value of n is from 0 to 30).
The "single bond" means that Si and Y 1 are directly connected (Y 1 -Si) without any element intervening, or Si and Y 2 are directly connected (Si-Y 2 ) it means.
Specifically, R 1 and R 2 may be an alkylene group having 1 to 5 carbon atoms or a single bond. More specifically, X 1, X 2, X 3, X 4, X 5, X 6 is an aryl group, X 1, X 2, C 1 -C 5 alkyl group or a group having 6 to 10 carbon atoms of X 3, X 4, X 5 , and X 6 may be an aryl group having 6 to 10 carbon atoms. More specifically, X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms, and X 1 , X 2 , X 3 , X 4 , 1, 2, 3 or 6 of X 5 and X 6 may be an aryl group having 6 to 10 carbon atoms. More specifically, X 1, X 2, X 3, X 4, X 5, X 6 is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, or naphthyl group, X 1, X 2, X 3 , One, two, three or six of X 4 , X 5 , and X 6 may be a phenyl group or a naphthyl group. and n may be an integer of 1 to 5.
For example, the silicon-containing monomer may be represented by any one of the following formulas (3) to (8)
(3)
≪ Formula 4 >
≪ Formula 5 >
(6)
≪ Formula 7 >
(8)
The silicon-containing monomer includes one or more substituted or unsubstituted aryl groups of 6 to 30 carbon atoms connected to the silicon, so that the conventional inorganic barrier layer and the organic barrier layer are deposited. In the organic light-emitting device encapsulation structure, An organic barrier layer having high resistance to plasma can be realized.
The silicon-containing monomer may have a molecular weight of from 100 g / mol to 2000 g / mol, specifically from 200 g / mol to 1000 g / mol. An organic barrier layer having a good deposition property and a low etching rate by plasma can be realized within the above range.
The silicone-containing monomer may be prepared by a conventional method, or a commercially available product may be used. For example, a silicone-containing monomer may be prepared by reacting a siloxane compound having at least one silicon-linked aryl group with a carbon-lengthening compound such as allyl alcohol and reacting (meth) acryloyl chloride, It does not. Alternatively, the silicon-containing monomer may be prepared by reacting (meth) acryloyl chloride with a siloxane compound having at least one silicon-linked aryl group, but is not limited thereto.
The silicon-containing monomers may be included singly or in combination of two or more.
The silicon-containing monomer may be present in the composition for encapsulating an organic light-emitting device in an amount of 10 wt% to 70 wt%, specifically 15 wt% to 50 wt%, more specifically 15 wt% to 15 wt%, based on the total weight of the photocurable monomer, 49% by weight. In the above range, the sealing composition can lower the outgas and the moisture permeability that can be generated from the plasma generated during the manufacture of the thin film encapsulation layer, and can realize an organic barrier layer having a small etching rate for plasma.
The sum of the photocurable monomer and the silicon-containing monomer may be 95 wt% or more, for example, 95 wt% to 99 wt%, based on the total weight of the photocurable monomer, the silicon-containing monomer, and the initiator. An organic barrier layer having a small etching rate for plasma in the above range can be realized.
Initiator
The initiator may include, without limitation, conventional photopolymerization initiators capable of carrying out photo-curable reactions. For example, the photopolymerization initiator may include triazine, acetophenone, benzophenone, thioxanthone, benzoin, phosphorus, oxime, or a mixture thereof.
The phosphorous can be diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, benzyl (diphenyl) phosphine oxide, or a mixture thereof. For example, when using a phosphorus initiator, the composition of the present invention may exhibit better initiation performance at long wavelength UVs.
The initiators may be included singly or in combination of two or more.
The initiator may be contained in the composition for encapsulating an organic light emitting device in an amount of 1 to 40 wt%, specifically 1 to 10 wt% based on the total weight of the photocurable monomer, the silicon-containing monomer and the initiator. In the above range, photopolymerization can sufficiently take place at the time of exposure, and the transmittance can be prevented from being lowered due to the unreacted initiator remaining after the photopolymerization.
The composition for encapsulating an organic light emitting element can be formed by mixing a photocurable monomer, a monomer containing silicon, and an initiator. For example, the composition for encapsulating an organic light emitting element can be formed into a solventless type solvent-free composition. For example, where the organic light emitting diode composition is a solventless type, wt% is based on the total weight of photocurable monomer, silicon containing monomer and initiator.
The composition for encapsulating an organic luminescent element is a photocurable composition which can be cured by irradiation at 10 to 500 mW / cm 2 for 1 second to 50 seconds at the UV wavelength.
The composition for encapsulating an organic luminescent element may have a photo-curing rate of 90% or more, specifically 90% to 99%, specifically 91 to 97%. In the above range, a layer in which a shift is not generated due to a low hardening shrinkage stress after curing can be used and used as an encapsulating device.
The composition for encapsulating an organic light emitting device may have a viscosity of 10 to 50 cps at 25 ± 2 ° C, and the sealing composition may be deposited in the above range.
The composition for encapsulating an organic luminescent element can have a transmittance of 95% or more, specifically 95 to 99% after curing. When the organic luminescent element is encapsulated in the above range, the visibility can be increased, and the transmittance can be measured in the visible light region Measured at a wavelength of 550 nm.
The composition for encapsulating an organic light emitting element may have a plasma etching rate after curing of 0% to 20%, specifically 0% to 15%. In the organic light-emitting device encapsulation structure in which the inorganic barrier layer and the organic barrier layer are formed in this order, the reliability of the organic light-emitting device can be improved.
The composition for encapsulating an organic luminescent element can be used for encapsulating an organic luminescent element. Specifically, an organic barrier layer can be formed in an encapsulation structure in which an inorganic barrier layer and an organic barrier layer are sequentially formed. In particular, the composition for encapsulating an organic light emitting device can be used in a flexible organic light emitting diode display.
The composition for encapsulating an organic light-emitting element is a member for a device, particularly a member for a display device, to a gas or a liquid in the surrounding environment, for example, oxygen and / or moisture in the air and / It can also be used as an encapsulation of a member for an apparatus which can be decomposed or become defective. For example, the member for the device may be an illumination device, a metal sensor pad, a microdisk laser, an electrochromic device, a photochromic device, a microelectromechanical system, a solar cell, an integrated circuit, a charge coupled device, a light emitting polymer, But are not limited thereto.
The organic light emitting diode display of the present invention may include an organic barrier layer formed of the composition for encapsulating an organic light emitting diode of the present invention. Specifically, the organic light emitting diode display includes an organic light emitting device, and a barrier stack formed on the organic light emitting device and including an inorganic barrier layer and an organic barrier layer, and the organic barrier layer is a composition for encapsulating an organic luminescent element As shown in FIG. As a result, the reliability of the OLED display device can be improved.
Hereinafter, an OLED display according to an embodiment of the present invention will be described with reference to FIG. 1 is a cross-sectional view of an OLED display device according to an embodiment of the present invention.
1, an organic light emitting
The
Although not shown in FIG. 1, the organic
The
The inorganic barrier layer is different in component from the organic barrier layer, so that the effect of the organic barrier layer can be compensated. The inorganic barrier layer may be formed of an inorganic material excellent in light transmittance and excellent in water and / or oxygen barrier properties. For example, the inorganic barrier layer may be a metal, a nonmetal, an intermetallic compound or alloy, an intermetallic compound or alloy, an oxide of a metal or a nonmetal, a fluoride of a metal or a nonmetal, a nitride of a metal or a nonmetal, A non-metallic oxygen nitride, a metal or non-metallic boride, a metal or non-metallic oxygen boride, a metal or a non-metal silicide, or a mixture thereof. The metal or base metal may be selected from the group consisting of Si, Al, Selenium, Zn, Sb, In, Ge, Sn, Bi, Metal, lanthanide metal, and the like, but are not limited thereto. Specifically, AlOx, comprising the inorganic barrier layer is a silicon oxide (SiOx), silicon nitride (SiNx), silicon oxygen nitride (SiOxNy), ZnSe, ZnO, Sb 2 O 3, Al 2 O 3 such as In 2 O 3, SnO 2 can be.
The inorganic barrier layer may be deposited by a plasma process, a vacuum process such as sputtering, chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma vapor deposition, and combinations thereof.
When the organic barrier layer is deposited alternately with the inorganic barrier layer, it is possible to secure the smoothing property of the inorganic barrier layer and to prevent the defect of the inorganic barrier layer from propagating to another inorganic barrier layer.
The organic barrier layer can be formed by a combination of coating, vapor deposition, curing, and the like of the composition for encapsulating an organic light emitting diode of the embodiment of the present invention. For example, the composition for encapsulating an organic light emitting element may be coated to a thickness of 1 to 50 탆 and cured by irradiation with 10 to 500 mW / cm 2 for 1 second to 50 seconds.
The barrier stack includes an organic barrier layer and an inorganic barrier layer, but the total number of organic barrier layers and inorganic barrier layers is not limited. The total number of organic and inorganic barrier layers may vary depending on the level of permeation resistance to oxygen and / or moisture and / or water vapor and / or chemicals. For example, the total number of the organic barrier layer and the inorganic barrier layer may be 10 or less, for example, 2 to 7, and specifically, the inorganic barrier layer / organic barrier layer / inorganic barrier layer / organic barrier layer / Barrier layer / organic barrier layer / inorganic barrier layer in this order.
In the barrier stack, the organic barrier layer and the inorganic barrier layer can be alternately deposited. This is due to the effect on the organic barrier layer produced due to the physical properties of the composition described above. As a result, the organic barrier layer and the inorganic barrier layer can complement or enhance the sealing effect on the device.
Hereinafter, an OLED display according to another embodiment of the present invention will be described with reference to FIG. 2 is a cross-sectional view of an OLED display device according to another embodiment of the present invention.
2, an
Hereinafter, the configuration and operation of the present invention will be described in more detail with reference to preferred embodiments of the present invention. It is to be understood, however, that the same is by way of illustration and example only and is not to be construed in a limiting sense.
Preparation Example 1: Preparation of silicon-containing monomer
To a 1000 ml flask equipped with a cooling tube and a stirrer was added 300 ml of ethyl acetate and 25 g of 3-phenyl-1,1,3,5,5-pentamethyltrisiloxane (Gelest) and 43 g of allyl alcohol And the mixture was purged with nitrogen for 30 minutes. Then, 72 ppm of Pt on carbon black powder (Aldrich) was added, the temperature in the flask was raised to 80 ° C, and the mixture was stirred for 4 hours. The residual solvent was removed by distillation. 71.5 g of the obtained compound was placed in 300 ml of dichloromethane, 39 g of triethylamine was added, and 34.3 g of acryloyl chloride was added slowly while stirring at 0 占 폚. The residual solvent was removed by distillation to obtain an HPLC purity of 97% as a compound of the following formula (molecular weight: 522.85 g / mol). (1H NMR: M, 4H;? 1.54, m, 4H;? 0.58, d, 2H;? 6.02, dd, 2H; m, 4H;? 0.02, m, 15H).
(3)
Production Example 2: Preparation of silicon-containing monomer
In Production Example 1, 21 g of 3,3-diphenyl-1,1,5,5-tetramethyltrisiloxane was used instead of 25 g of 3-phenyl-1,1,3,5,5-pentamethyltrisiloxane (Molecular weight: 584.92 g / mol) was obtained in the same manner as in Example 1, except that 30.2 g of methacryloyl chloride was used instead of 34.3 g of acryloyl chloride. (1H NMR d, 2H, d, 2H, d, 2H, d, 2H, d, 2H, M, 4H;? 1.52, m, 4H;? 0.58, m, 4H;? 0.04, m, 12H).
≪ Formula 4 >
Preparation Example 3: Preparation of silicon-containing monomer
In Production Example 1, 21 g of 1,3,5-triphenyl-1,3,5-trimethyltrisiloxane was used instead of 25 g of 3-phenyl-1,1,3,5,5-pentamethyltrisiloxane, (Molecular weight: 646.99 g / mol) represented by the following formula (5) was obtained with the HPLC purity of 94%, except that 31 g of methacryloyl chloride was used instead of 34.3 g of roile chloride. (1 H NMR:? D, 2H,? 5.82, t, 1H;? 5.59, d, 2H,? 3.86, d, 2H, m, 4H;? 1.52, m, 4H;? 0.58, m, 4H;? 0.16, m, 9H).
≪ Formula 5 >
Preparation Example 4: Preparation of silicon-containing monomer
In Production Example 1, 19 g of 1,1,3,3,5,5-hexaphenyltrisiloxane was used instead of 25 g of 3-phenyl-1,1,3,5,5-pentamethyltrisiloxane, In the same manner as in Example 1 except that 30 g of methacryloyl chloride was used instead of 34.3 g of dichloromethane, the following compound of Formula 6 was obtained with an HPLC purity of 92% (1 H NMR: 隆 7.59 to 7.12, m, 30H; M, 4H;? 1.52, m, 4H;? 0.58, d, 2H;? 6.02, dd, 2H;? 5.82, m, 4H;).
(6)
Specific specifications of the components used in Examples and Comparative Examples are as follows.
(A1) tetraethylene glycol diacrylate, (A2) decanediol diacrylate, (A3) pentaerythritol tetraacrylate (available from Aldrich)
(B2) the monomer of Production Example 2, (B3) the monomer of Production Example 3, (B4) the monomer of Production Example 4 (B)
(C) Initiator: Darocur TPO (BASF)
(D) a monomer represented by the following formula (9) (molecular weight: 460.78 g / mol, X-22-164,
≪ Formula 9 >
Example 1
(A1) 20 parts by weight of tetraethylene glycol diacrylate, 45 parts by weight of (A2) decanediol diacrylate, (B1) 30 parts by weight of the monomer of Preparation Example 1, and 5 parts by weight of the initiator (C) And mixed at room temperature for 3 hours using a shaker to prepare a sealing composition (25 cps at 25 캜).
Examples 2 to 8 and Comparative Examples 1 to 3
Example 1 was repeated except that the kind and / or the content of the photocurable monomer (A) and the type and / or the content of the silicon-containing monomer (B) in Example 1 were changed as in the following Table 1 (unit: To prepare a sealing composition.
Comparative Example 4
A sealing composition was prepared in the same manner as in Example 1, except that 30 parts by weight of the monomer (D) was used instead of 30 parts by weight of the monomer (B1) of Production Example 1 in Example 1.
The sealing compositions prepared in Examples and Comparative Examples were measured for physical properties shown in the following Table 1, and the results are shown in Table 1.
(%)
As shown in Table 1, the composition for encapsulating an organic light emitting diode of the present invention can realize an organic barrier layer having a high photo-curability and a high light transmittance and a low etching rate against plasma.
On the other hand, the compositions for encapsulating organic light emitting devices of Comparative Examples 1 to 3 which did not contain the silicon-containing monomer of the present invention had a low photo-curability and a high etching rate against plasma.
In addition, Comparative Example 4 including a silicon-containing monomer containing no aryl group had a lower photo-curability and a lower etching rate with respect to plasma than those of Comparative Examples 1 to 3, but the etching rate was measured to be higher than those of Examples 1 to 8 containing an aryl group . .
(1) Plasma etching rate: An organic barrier layer was formed by depositing and photo-curing a sealing composition on a Si wafer. The initial deposition height (T1, unit: 占 퐉) of the organic sealing layer was measured by photocuring. ICP plasma (ICP) plasma was applied to the organic barrier layer by ICP CVD (BMR Technology) at an ICP power of 2500 W, a RE power of 300 W, a DC bias of 200 V, an Ar flow of 50 sccm, an ethching time of 1 min and a pressure of 10 mTorr After the treatment, the height (T2, unit: 占 퐉) of the organic barrier layer was measured. The etch rate of the organic barrier layer by plasma was calculated by Equation (1). The height (thickness) of the organic barrier layer was measured by FE-SEM Hitachi High Technologies Corporation.
<Formula 1>
Etching rate (%) of organic barrier layer by plasma = (T1-T2) /
(2) Light transmittance: A film having a thickness of 10 탆 was prepared by UV curing the composition for encapsulation under N 2 condition, and the transmittance of the film was measured with a Lambda 950 (Perkin Elmer) at a wavelength of 550 nm in a visible light region.
(3) photo-ratio: the intensity of the absorption peak in the FT-IR (NICOLET 4700, Thermo Co.) to the vicinity of 1635cm -1 (C = C), 1720cm -1 vicinity (C = O) with respect to the composition for sealing . The composition for sealing is applied on a glass substrate by spraying and irradiated for 10 seconds at 100 mW / cm 2 to be UV-cured to obtain a specimen of 20 cm x 20 cm x 3 m (width x length x thickness). Obtain a cured film and, FT-IR (NICOLET 4700, Thermo Co.) is used in the vicinity of 1635cm -1 (C = C), 1720cm -1 measured intensity of the absorption peak in the vicinity of the (C = O) a. The photo-curing rate is calculated according to the following formula (2).
<Formula 2>
Photocuring rate (%) = | 1- (A / B) | x 100
(In the above formula 2, A is the ratio of the intensity of the absorption peak at about 1635 cm -1 to the intensity of the absorption peak at about 1720 cm -1 for the cured film,
B is the ratio of the intensity of the absorption peak near 1635 cm -1 to the intensity of the absorption peak near 1720 cm -1 for the sealing composition).
It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (12)
Wherein the silicon-containing monomer is represented by the following formula (1)
≪ Formula 1 >
(Wherein R 1 and R 2 are the same or different and each represents a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted alkylene ether group having 1-30 carbon atoms, Wherein R 'is a substituted or unsubstituted alkyl group having 1-30 carbon atoms, and R "is a substituted or unsubstituted alkylene group having 1-20 carbon atoms, A substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylene group having 7 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 7 to 30 carbon atoms, or * -OR " Or an unsubstituted or substituted alkylene group having 1-20 carbon atoms)
X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are the same or different and represent hydrogen, a substituted or unsubstituted alkyl group having 1-30 carbon atoms, a substituted or unsubstituted alkyl ether group having 1-30 carbon atoms , * -N (R ') (R ") wherein * is the connecting site of the element, R' and R" are the same or different and represent hydrogen or a substituted or unsubstituted alkyl group having 1-30 carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms,
At least one of X 1 , X 2 , X 3 , X 4 , X 5 and X 6 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Y 1, Y 2 are the same or different, to a (2),
(2)
(Wherein, * is the connecting site of the element and Z is hydrogen or a substituted or unsubstituted alkyl group having 1-30 carbon atoms)
n is an integer from 0 to 30, or the average value of n is from 0 to 30)
The composition for encapsulating an organic luminescent element has an etching rate of the organic barrier layer of 0 to 20% by plasma of the following formula 1 after photo-curing,
<Formula 1>
Etch rate of organic barrier layer by plasma = (T1-T2) / T1 x 100
T1 is an initial deposition height (unit: 占 퐉) of the organic barrier layer obtained by depositing and photo-curing the composition for encapsulating an organic light emitting element on a Si wafer,
T2 shows the organic barrier layer after ICP power of 2500 W, RE power of 300 W, DC bias of 200 V, Ar flow of 50 sccm, ethching time of 1 min, pressure of 10 mtorr, Height (unit: 占 퐉)),
The photocurable monomer may be at least one monomer selected from the group consisting of 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, octanediol di (meth) acrylate, nonanediol di Acrylate, di (meth) acrylate, undecanediol di (meth) acrylate, and dodecanediol di (meth) acrylate.
(3)
≪ Formula 4 >
≪ Formula 5 >
(6)
≪ Formula 7 >
(8)
And a barrier stack formed on the organic light emitting device and including an inorganic barrier layer and an organic barrier layer,
Wherein the organic barrier layer is formed of the composition for encapsulating an organic light emitting diode according to any one of claims 1 to 5, 10 and 11.
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| Application Number | Priority Date | Filing Date | Title |
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| EP15161125.8A EP2924085B1 (en) | 2014-03-28 | 2015-03-26 | Composition for encapsulation of organic light emitting diode and organic light emitting diode display manufactured using the same |
| JP2015067095A JP6852960B2 (en) | 2014-03-28 | 2015-03-27 | Composition for encapsulating organic light emitting element and organic light emitting display device |
| CN201510142313.5A CN104953042B (en) | 2014-03-28 | 2015-03-27 | The constituent of encapsulating organic light emitting diode and the display manufactured using it |
| US14/671,110 US9893307B2 (en) | 2014-03-28 | 2015-03-27 | Composition for encapsulation of organic light emitting diode and organic light emitting diode display manufactured using the same |
| TW104110266A TWI617610B (en) | 2014-03-28 | 2015-03-30 | Composition for encapsulation of organic light emitting diode and display manufactured using the same |
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| KR101835941B1 (en) | 2015-10-19 | 2018-03-08 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same |
| KR101778864B1 (en) * | 2015-12-23 | 2017-09-14 | 엘지전자 주식회사 | Light converting member, light emitting package device and display device comprising the same |
| JP6481647B2 (en) * | 2016-03-22 | 2019-03-13 | 信越化学工業株式会社 | Ultraviolet curable silicone composition, cured product thereof, optical element sealing material comprising the composition, and optical element sealed with the optical element sealing material |
| KR102008184B1 (en) * | 2016-11-11 | 2019-08-07 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same |
| CN111788265B (en) * | 2017-04-21 | 2024-04-23 | 柯狄公司 | Compositions and techniques for forming organic thin films |
| CN111094483A (en) | 2017-08-31 | 2020-05-01 | 三星Sdi株式会社 | Adhesive film and optical member including the same |
| WO2020059650A1 (en) * | 2018-09-20 | 2020-03-26 | 信越化学工業株式会社 | Uv curable silicone composition and cured product thereof |
| KR102444454B1 (en) * | 2019-06-03 | 2022-09-16 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diode device and organic light emitting diode display using prepared the same |
| KR102541647B1 (en) * | 2020-02-18 | 2023-06-08 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same |
| KR102430601B1 (en) | 2020-03-03 | 2022-08-08 | 삼성에스디아이 주식회사 | Adhesive film, optical member comprising the same and optical display apparatus comprising the same |
| KR102301804B1 (en) * | 2020-04-06 | 2021-09-13 | 한남대학교 산학협력단 | A photocurable composition for sealing organic light emitting device |
| KR102527459B1 (en) | 2020-05-29 | 2023-04-28 | 삼성에스디아이 주식회사 | Adhesive protective film, optical member comprising the same and optical display apparatus comprising the same |
| KR20220168666A (en) * | 2021-06-17 | 2022-12-26 | 삼성에스디아이 주식회사 | Composition for encapsulating organic light emitting diodes and organic light emitting diodes display comprising organic layer prepared using the same |
| CN114015277B (en) | 2021-10-19 | 2023-05-12 | 杭州福斯特电子材料有限公司 | Ink composition for OLED packaging and application thereof |
| CN115109464B (en) * | 2022-07-06 | 2023-07-14 | 杭州福斯特应用材料股份有限公司 | Ink composition, package structure and semiconductor device |
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| JP2009032679A (en) * | 2007-06-28 | 2009-02-12 | Semiconductor Energy Lab Co Ltd | Light-emitting device, light-emitting apparatus, electronic equipment, and manufacturing method of light-emitting device |
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| US6450642B1 (en) * | 1999-01-12 | 2002-09-17 | California Institute Of Technology | Lenses capable of post-fabrication power modification |
| JP2009016672A (en) * | 2007-07-06 | 2009-01-22 | Tokyo Electron Ltd | Manufacturing method of semiconductor device, semiconductor device, semiconductor manufacturing device, and storage medium |
| JP5216343B2 (en) * | 2008-01-30 | 2013-06-19 | クラレノリタケデンタル株式会社 | Polymerizable monomer suitable for dental materials |
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| JP2012014930A (en) * | 2010-06-30 | 2012-01-19 | Sanyo Chem Ind Ltd | Photosensitive resin composition |
| JP5562739B2 (en) * | 2010-06-30 | 2014-07-30 | 三洋化成工業株式会社 | Photosensitive resin composition |
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| US20130236681A1 (en) * | 2012-03-06 | 2013-09-12 | Chang Min Lee | Photocurable composition, barrier layer including the same, and encapsulated apparatus including the same |
| JP5989417B2 (en) * | 2012-06-20 | 2016-09-07 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Ultraviolet curable silicone resin composition and image display device using the same |
| KR101600653B1 (en) * | 2012-12-26 | 2016-03-07 | 제일모직주식회사 | Composition for encapsulation, barrier layer comprising the same and encapsulated apparatus comprising the same |
| KR101696965B1 (en) * | 2013-06-27 | 2017-01-16 | 제일모직주식회사 | Photocurable composition and encapsulated apparatus comprising the same |
| KR20140034882A (en) * | 2014-02-14 | 2014-03-20 | 에스엠에스주식회사 | Preparation of new silicone diacrylate and its photosensitive resin composition |
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